


Win

by YlvaUllsdotter



Category: Supernatural
Genre: Angst, Dean x Lisa - Freeform, Dean x Reader, F/M, Reader Insert, SPN - Freeform, Second Chances, Supernatural - Freeform, Winner Takes It All, dean is a dumbass, season 13, season 6
Language: English
Status: Completed
Published: 2018-08-08
Updated: 2018-08-08
Packaged: 2019-06-23 19:23:02
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,897
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15613248
Author URL: https://archiveofourown.org/users/YlvaUllsdotter/pseuds/YlvaUllsdotter
Summary: Your love affair with Dean Winchester burned hot and fast that summer six years ago, until he had to leave for New Orleans. He made no promises, but you still had expected him to return. A year later you gave up waiting. The not knowing what happened to him ate at you, and you avoided relationships like the plague ever since. Until you stopped at a small bar in Cicero, Indiana, and saw Dean Winchester, alive and well, and apparently on a date.





	Win

**Author's Note:**

> Written for Jill’s ([@sis-tafics](https://sis-tafics.tumblr.com/)) 8k Musical Challenge. My prompt was the song The Winner Takes It All from the musical Mamma Mia. It takes place a few months before season 6 started, on Valentine’s Day, with flashbacks to the job Dean worked in New Orleans before he went to get Sam at Stanford, and ends mid-season 13. It’s angst. I apologize for nothing.

You caught the bartender’s attention, tapped the rim of your shot glass silently, and waited while he filled it to the brim once again. You had lost count somewhere around half a dozen, but it was of little consequence. After so many years, you had built up a tolerance and so far you were only pleasantly buzzed. 

Sitting at the far end of the bar, you had chosen to endure the coming and going to the restrooms behind you in favor of being able to see the entrance. Most people would call you paranoid, but paranoia had kept you alive so far so you were unlikely to stop anytime soon. 

As you lifted the glass and tipped your head back to down the amber liquid, you saw the door opening. People had been coming and going all evening, but you were people watching and liked to get a good look. Setting your glass back on the counter, you saw a man with his back turned your way as he held the door for a pretty brunette who smiled at him. He turned and fell in beside her naturally and you noticed every detail in less time than it took your brain to process what you had actually seen.

They were both wearing denim and flannel, her in sneakers while he wore work boots of scuffed brown leather. She was actually more than just pretty, with wavy dark brown hair. From that distance, you were unable to make out her eyes, but you were willing to bet they were brown. Her face was turned towards him, her full lips moving as she was saying something and he looked down at her with a soft smile, his green eyes full of affection.

You started to feel light-headed, gasping for air like a fish out of water, as you realized who you were looking at. There, apparently on a date, was someone you had thought dead for six years. 

Dean Winchester.

Without any conscious thought on your part, your mind flashed back to that summer six years ago.

* * *

_ It had been hotter than Satan’s asshole when you got to that small town in west Texas and you had cursed yourself for ever picking up that particular hunt. It looked like a simple salt-n-burn, and you hoped to be out of there in a day, two at most, and head back to cooler climates. Canada sounded nice about then. Or maybe Alaska. _

_ Your sour mood had only gotten worse when you had run into Dean Winchester, hunting your ghost. His charm and wit had quickly changed your mind, however, and you ended up partnering with him on the hunt, finishing up that same evening. Both of you had wanted to celebrate, and perhaps also get to know each other a little better, and you had found yourselves at the only bar in town. _

_ The bar had been dingy, the whiskey cheap, but the company made up for it. You had stayed until closing time, then gone back to your motel room where you spent the rest of the night getting to know each other in the biblical sense. _

_ Dean had been waiting for word from his dad for where to go next, and you had nothing better to do, so you both ended up staying in that small town for two full months. It was the happiest time of your life, and you had thought it had meant something to Dean as well.  _

_ In mid-October, Dean had finally heard from his dad, some hunt in New Orleans, and he took off, but not before telling you he cared about you. It was Dean Winchester, and in the past few weeks, you had learned that he was less than eloquent with his words. You accepted him as he was, quirks and trust issues and all. The two of you had shared a passionate kiss in the motel parking lot before he got in his Impala and drove off. _

* * *

You blinked a few times to clear the memories from your vision, noticing that Dean and his date were seated at one of the booths along the wall, each of them with a glass of beer. With the distance between you, and the din of the bar, there was no way you could make out what they were saying, but their expressions said it all really. They were two people very much in love with each other. Every so often one of them would reach over and touch the other, just small touches, fingers brushing the back of a hand, a hand laid softly on a forearm, a strand of hair tucked behind an ear. All of that, along with the way they looked at each other, told you that this was a relationship that was comfortable, it was not new.

Still feeling a little short of breath, you watched them without appearing to stare, your glass forgotten on the counter in front of you. You knew that you had no right to feel jealous, Dean had never made any promises. You were the one who had stupidly waited around in that small town for over a month, hoping to hear from him. You were the one who had imagined feelings where there apparently had been none. You were the one who had driven out of that small town leaving behind a broken heart and the memories of a pair of green eyes. 

That was when your caution had turned to paranoia. Ever since then you had only had one-night-stands, never staying around long enough for anything more. In fact, you had preferred the company of women over men, because no man could ever compare.

Your breath caught in your throat as you watched Dean stand up, his hand brushing the woman’s shoulder lightly before he turned and walked towards you. His eyes met yours for the briefest moment as he passed by on his way to the restrooms. You refused to turn around to watch him, so you missed the small frown as he turned before slipping through the door, giving you a thoughtful look.

Your whole body was tense, your ears primed to listen for his footsteps as he returned to his table. Except those steps stopped behind you, then switched directions to come up next to you. He leaned on the counter and signaled his order for two more beers to the bartender, then turned to you with a small smile on his plump lips.

“I’m sorry, this is gonna sound really cheesy, and I’m not trying to pick you up, but have we met before?” His tone was both apologetic and amused as if he knew it was a silly question, but he had to ask it.

You shrugged and cleared your throat. “I dunno, have we?” You replied, trying to keep your voice neutral.

Dean’s green eyes studied your face, even as the bartender set two fresh beers in front of him, and suddenly widened in shock.

"Y/N?” His voice had dropped to just above a whisper, and you could barely make it out over the noise of the bar.

You swallowed hard and nodded, your own eyes drawn in by his, unable to look away. 

“Well, damn. I...I don’t know what to say,” Dean stated, sounding deflated.

“There’s nothing to say, is there?” You retorted, surprised by how small and hurt your voice came out. You pointedly tore your eyes from Dean’s and looked over at his date, prompting him to glance over his shoulder.

“Uhm, yeah, I...should go,” he managed and grabbed the glasses. He paused for a moment, then his eyes found yours again. “I’m sorry,” was all he said before turning and walking back to the table where his date greeted him with a warm smile.

Your heart, which had been shattered six years ago and put back together over time, once again lay in pieces. Dropping a twenty on the counter, you slunk out of the bar without looking over at Dean and his date. In a sort of numb haze, you got in your car and drove back to your motel where you went through your evening ritual of salting the door and windows before undressing and getting into bed with your favorite silver blade under your pillow.

Without anything else to occupy it, your mind went back to the conversation at the bar and you felt the prickling of tears welling up in your eyes. There was nothing you could do to stop them, and before you knew it you were curled in a fetal position, pressing a pillow to your face to muffle your sobs.

The next morning, you packed up your car and left town, a brand new lid put over your emotions. 

For the next seven years, you were like a machine, hunt, sleep, eat, drink, rinse and repeat. Apocalypses came and went and the world kept on spinning. You heard stories of the Winchesters from other hunters, but most of them were too incredible to possibly be true. Each time Dean was mentioned, a numbness spread through you and you quickly found a way to change the subject. 

The last you had heard, the Winchesters, along with a handful of other hunters, had taken down the British Men of Letters. Their representative had approached you too, and you had listened in silence before turning them down. High tech toys were probably nice, but you preferred the honest weight of a gun or blade in your hand, and the smell of monster blood in your nostrils. Not to mention they all seemed shady as hell.

You had heard the Winchesters worked mostly the midwest these days, so you had kept away from that general area for years until a very good friend called you for help with a particularly nasty poltergeist. There was no way for you to say no without sounding like a complete asshat so here you were in a small town outside of Wichita, Kansas.

The hunt had been mostly successful. You had both sustained some minor injuries when the poltergeist started hurling furniture around, but nothing that needed stitches. Bandaged up, you headed to the nearest bar for a drink or five to celebrate. With your friend occupying you as you entered, you failed to scan the bar as you used to, seating yourselves in a booth while still discussing particulars of the hunt.

You were so engrossed in your conversation, you neglected to look up even as someone placed a pair of beer bottles on the table, simply grabbing one of them and taking a swig. Except, as you raised the bottle to drink, your eyes caught the face that was attached to the arms that brought the beer and you almost choked.

_ Dean Winchester. _

Spluttering, you wiped your face with the sleeve of your ever-present flannel shirt and stared at Dean. “What are you doing here?”

Dean gave that crooked smile that had made you fall in love with him all those years ago. His hand came up to rub the back of his neck and he looked a bit sheepish. 

“Uhm, well, I was just hanging out when I saw you come in,” he replied, and you could have sworn the tips of his ears turned red. He glanced at your friend briefly before his eyes returned to you. “How have you been, Y/N?”

You barely registered your friend when she excused herself, obviously catching on to the tension between you and Dean. He slid into the booth after she left, his eyes never leaving yours.

Taking a deep breath to remind yourself that your lungs actually needed you to suck down air to avoid you passing out, you leaned back in your seat. “Fine. I’ve been fine, Dean,” you finally managed, when your brain remembered that he had asked you a question.

Dean nodded, still unable to take his eyes off you. “I’m glad. I’ve thought about you when I wasn’t trying to stop one apocalypse or another. I felt really bad about the last time we met.”

It was your turn to nod. “Yeah, well, you certainly took me by surprise. I thought you were dead,” you retorted, your tone carefully neutral.

“Oh.” He cleared his throat. “Yeah, uhm, I can see how you might have thought that. I didn’t exactly let you know what happened,” he mumbled.

You shrugged slightly. “You made no promises, Dean,” you told him as you picked up your bottle and took a drink.

Dean shifted a little in his seat, looking uncomfortable. “No, no I didn’t, but it was still a dick move. I don’t really have an excuse except I was young and stupid and didn’t realize what I had until I didn’t have it anymore.”

Taking another drink from your bottle, you sat in silence, waiting to see if Dean would say anything else.

“I’m sorry. Really. I tried to find you after…,” he paused and shrugged, “it doesn’t really matter. But I did look for you. You’re just really good at staying under the radar.” He gave you a small smile that expressed his admiration for your skills. 

You set the bottle down on the table and leaned forward, resting your forearms on the varnished wood. With your eyes still on Dean’s, your fingers blindly picked at the label on the bottle. 

“What about…,” you trailed off, looking at him pointedly.

“Lisa?” He shook his head, a look of hurt sadness crossing his face. “No, she’s not in the picture anymore.”

You would have asked more, but he clearly had no desire to talk about it so you let it drop. When the silence extended between you, Dean felt the need to fill it.

“So, uhm, I don’t know if you heard, but Sam and I kinda live around here now,” he started.

You nodded and your hands stilled. “Yeah, I heard. It’s why I’ve kept to the southwest and the west coast mainly the past few years.”

“Oh.” Dean sounded as if he had no idea what to do with that information. His fingers idly traced patterns in a puddle of condensation left behind by your friend’s bottle on the tabletop, his eyes finally breaking contact and studying those patterns as if they were the most interesting thing on the planet. 

You studied Dean in turn while he was preoccupied, noting the differences in his appearance. He looked mostly the same, just older. There were a few wrinkles but no gray hairs yet. If anything, the changes made him more handsome and the sight of him had that lid on your emotions buckling under the pressure.

Still looking down at his fingers, Dean cleared his throat, pulling you from your thoughts. “I know that...I really hurt you, Y/N, and I just wanna say I’m so sorry about that.” He looked up again, his green eyes finding yours. “When you walked in here tonight, I felt like I was given a second chance, to make things right. I won’t blame you if you hate me and want nothing to do with me, but on the off chance that you don’t, I’d really like the chance to start over.” His look was almost pleading when he stopped talking, his hands had stilled on the table and he was waiting for you to respond.

Taking another drink from your bottle, mainly to break the eye contact for a moment, you set the bottle back down and took a deep breath. “I don’t know if I can trust you, Dean. What you did, disappearing without a trace like that, it broke me. I spent years putting myself back together, only to have to start all over after...that night,” you tried to explain. When Dean opened his mouth as if to speak, you held your hand up to stop him. “You’ve already apologized, Dean, and I accept your apology, but it’s gonna take a lot more for me to trust you again. Hell, I don’t trust anyone anymore.”

Dean hung his head and looked up at you through his lashes. “Will you at least stick around and give me a chance to earn your trust?”

You thought about it for a long time while Dean sat quietly and waited for your decision. Draining the last of the beer, you set the bottle down and shrugged. “I’ll think about it,” you said as you stood from your seat and looked down at him. “No promises.”

Dean nodded. “That’s fair. Sam and I are living out of an old Men of Letters bunker outside Lebanon. You won’t be able to find it on your own, but if you want, call me and you’re welcome to come by anytime.” He quickly scribbled his number on a stray napkin and handed it to you.

You took the napkin and stuck it in your pocket without looking at it. “No promises,” you repeated, giving Dean a pointed look before you turned and walked away. Your friend had left you a text message that she had gone back to the motel and you decided to do the same. Your composed demeanor while talking to Dean had after all been just a sham. You were shaken to your core and you needed time to process. 

Maybe, just maybe, you could have a win for once.


End file.
